Triphenylantimony

Triphenylantimony appears as off-white powder that are stable in air. It is soluble in most organic solvents and slightly soluble in ethanol, but remains insoluble in water. The melting point is 50 °C (within a 46–63 °C range), and the boiling point is 377 °C with decomposition. It is classified as toxic and an irritant.

Stibonium salts, cocatalyst in converting trienes to aromatics and hydroaromatics, react with nitricsulfuric acid to give trinitro derivatives, polymerization inhibitor, lubricating-oil additive.

Under atmospheric conditions and at room temperature, a solution of furfuryl acetal (500 mg, 2.6 mmol) and triphenylantimony (92 mg, 0.3 mmol) in dichloromethane (10 mL) was stirred for 17 hours. The reaction mixture was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 3:1, Rf = 0.36) to afford a yellow solid, furfuryl acetic acid (466 mg, 94% yield).

Triphenylantimony dichloride was prepared by direct chlorination of triphenylantimony in petroleum ether or by reaction with aluminium trichloride (or iron(III) chloride) in chloroform.

Atomic number of base material: 51 Antimony

core: antimony
reagent type: catalyst

Poison by ingestion and intraperitoneal routes. Flammable when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, use water, foam, mist. When heated to decomposition it emits toxic fumes of Sb. See also ANTIMONY COMPOUNDS.

Recrystallise Ph3Sb from acetonitrile [Hayes et al. J Am Chem Soc 107 1346 1985]. [Beilstein 16 H 891, 16 IV 1198.]

[1] Yasuike, S., Kishi, Y., Kawara, S.-I., & Kurita, J. (2005). Catalytic action of triarylstibanes: oxidation of benzoins into benzyls using triarylstibanes under an aerobic condition. Chemical & Pharmaceutical Bulletin, 53 4, 425–427. https://doi.org/10.1248/cpb.53.425